Of the few guides/manuals/histories acting as deconstruction of a genre that I've read over the last few years (and both the online and real-world bookshelves are beginning to swell with them), I've sussed out two very clear approaches which work with varying degrees of success: on one side, you have the type that exists absolutely inside the fiction and doesn't acknowledge the reader or that it's fiction at all (Max Brooks' World War Z being the prime recent example here); Matt D. Wilson's The Supervillain Handbook: The Ultimate How-to Guide to Destruction and Mayhem, is a hybrid of that other sort, where the writer not only acknowledges the reader (the "author" of the book, King Oblivion, PH.D frequently calls out the would-be villains reading his guide), but actually draws attention to the popular fiction that inspired it.
Wilson, a regular contributor to Cracked.com, borrows from that site's style of list-style posts, breaking down the chapters in The Supervillain Handbook into numbered how-to's about picking one's costume, choosing a nemesis, finding the right henchmen, and even the different motivations for becoming someone who screams at someone else from the lip of an active volcano while wearing a cape. Wilson's King Oblivion is a member of the International Society of Supervillains (also a thing online), and he speaks to the reader in a mixture of Silver Age bluster and collected self-help speak (one helpful tip in finding a suitable nemesis: "Match your aptitude"). The character's voice is funny, albeit in short bursts (handily, the chapters are short enough where you can choose to hang with King Oblivion at your own easy pace).
As for insights into comic book-style villainy and as far as a trenchant deconstruction of that style character, The Supervillain Handbook does alright, referencing characters created by Wilson as well as a few from the Big Two to make the overall point that you have to be crazy to take that particular gig. Even King Oblivion is not immune to the occasional outburst at the reader, warning them of the consequences of say, copyright infringement of his protected material.
One of the real pleasures of the book are the little sidebars detailing existing lame comic villains, their origins, and how they utterly fail to make it big. An interesting note about these: Wilson must be a big Spider-Man fan, as he draws more than a few of his examples from that particular character's colorful rogues gallery. Wilson also uses sidebars featuring real historical figures who may or may not have been supervillains, but these are a little less successful, relying on such gems as "The Hanna-Barbera guys hypnotized children with repeated frames of animation." The problem is that these just don't draw on anything interesting or strange about these real figures and simply invents something out of whole cloth to hang the villain label on.
Illustrations are provided by Adam Wallenta, and they're workable if unexceptional--I kept thinking of the sort of build-a-character templates for MMOs when looking at his art. Really, this is kind of appropriate for a book that's about building yourself up as a supervillain, and thinking on it more, the style serves the book well.
The Supervillain Handbook is available now both in print and digitally through Skyhorse Publishing.